Synthesis, Crystal Structure and Biological Activity of Diethyl 1,4-dihydro-2,6-dimethyl-4-(4-methyl-1,2,3-thiadi azol-5-yl)pyridine-3,5-dicarboxylate

【摘要】 The title compound diethyl 1,4-dihydro-2,6-dimethyl-4-(4-methyl-1,2,3-thiadiazol-5-yl) pyridine-3,5-dicarboxylate(C16H21N3O4S, Mr = 351.42) was prepared by the Hantszch reaction with 4-methyl-1,2,3-thiadiazole-5-formaldehyde, ethyl acetoacetate and ammonium acetate in the presence of aluminum chloride in alcohol, and its structure was characterized by IR spectra, 1H-NMR, EA, and single-crystal X-ray diffraction. The crystal of the title compound belongs to monoclinic system, space group P21/n with a = 11.300(2), b = 12.771(3), c = 12.826(3) ?, β = 96.55(3)o, V = 1839.0(6) ?3, Z = 4, Dc = 1.296 g/cm3, μ(MoKa) = 0.71073 mm-1, F(000) = 744, R = 0.0981 and wR = 0.1994. X-ray diffraction result shows that the torsion angles of N(1)–C(2)– C(3)–C(4) and C(2)–C(3)–C(4)–C(8) are 178.9(3)° and –130.3(3)°, respectively. All rings in the title compound are non-planar. The bioassay results indicate that the title compound has good fungicidal activity, good antivirus activity against tobacco mosaic virus and certain extent of insecticidal activity against Mythimna separata.更多还原

【Abstract】 The title compound diethyl 1,4-dihydro-2,6-dimethyl-4-(4-methyl-1,2,3-thiadiazol-5-yl) pyridine-3,5-dicarboxylate(C16H21N3O4S, Mr = 351.42) was prepared by the Hantszch reaction with 4-methyl-1,2,3-thiadiazole-5-formaldehyde, ethyl acetoacetate and ammonium acetate in the presence of aluminum chloride in alcohol, and its structure was characterized by IR spectra, 1H-NMR, EA, and single-crystal X-ray diffraction. The crystal of the title compound belongs to monoclinic system, space group P21/n with a = 11.300(2), b = 12.771(3), c = 12.826(3) ?, β = 96.55(3)o, V = 1839.0(6) ?3, Z = 4, Dc = 1.296 g/cm3, μ(MoKa) = 0.71073 mm-1, F(000) = 744, R = 0.0981 and wR = 0.1994. X-ray diffraction result shows that the torsion angles of N(1)–C(2)– C(3)–C(4) and C(2)–C(3)–C(4)–C(8) are 178.9(3)° and –130.3(3)°, respectively. All rings in the title compound are non-planar. The bioassay results indicate that the title compound has good fungicidal activity, good antivirus activity against tobacco mosaic virus and certain extent of insecticidal activity against Mythimna separata.更多还原